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Soluble polythiophene derivatives

a technology of polythiophene and derivatives, which is applied in the field of soluble polythiophene derivatives, can solve the problems of limiting the practicability of optoelectronic devices made of polymer semiconducting materials and reducing the power conversion efficiency of oscs, and achieves the effects of improving the degree of intramolecular conjugation and intermolecular - interaction, and increasing carrier mobility

Active Publication Date: 2009-12-03
IND TECH RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0012]An object of the present invention is to provide a soluble polythiophene derivative containing highly coplanar repeating units. The coplanar characteristic of the TPT (thiophene-phenylene-thiophene) units improves the degree of intramolecular conjugation and intermolecular π-π interaction, further increasing carrier mobility.

Problems solved by technology

However, a main drawback for conjugated polymer applicability in optoelectronic devices is its low carrier mobility, consequently limiting the practicability of optoelectronic devices made with polymer semiconducting material.
Otherwise, if the electrons and holes recombine, the carrier function will disappear, thus reducing power conversion efficiency of the OSCs.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparative Example 1

Synthesis of p-thiophene-phenylene-thiophene (S2)

[0042]

[0043]Scheme1 depicts the synthesis of compound S2 (p-TPT). Compound 8 was prepared by the synthetic method described in Org. Lett. 2006, 8, 5033-5036. 626 mg (1 mmol) of Compound 8 and 392 mg (2.2 mmol) of N-bromosuccinimide (NBS) were dissolved in 20 mL of chloroform in a 100 mL two-necked bottle. The bottle was wrapped by Al foil and kept under N2 atmosphere overnight. The organic phase was extracted by a chloroform and saturated sodium chloride solution. Next, the organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated on a rotary evaporator. A pale yellow solid S2 was obtained after precipitation by methanol.

[0044]NMR data of the compound S2 was as follows.

[0045]1H NMR (CDCl3, 200 MHz) δ 2.29 (s, 12H), 6.94 (s, 2H), 7.05˜7.12 (m, 16H), 7.29 (s, 2H).

Preparative Example 2

Synthesis of m-thiophene-phenylene-thiophene (S3)

[0046]

[0047]Scheme 2 depicts the synthesis of compoun...

example

Example 1

Synthesis of Polymer P6

[0067]

[0068]Scheme 7 depicts the synthesis of compound P6. 0.3 mmol of p-TPT, 5.5 mg (2 mol %) of 5,5′-bis-trimethylstanny 4,4′-bis(dodecyl)-2,2′-bithiophene, 14.6 mg (16 mol %) of tri(o-tolyl)phosphine and 5 mL of chlorobenzene were placed in a glass flask. After deoxygenation, the flask was placed in a microwave reactor (640 W, 30 min) for polymerization. After cooled to room temperature, the reaction mixture was added to methanol for precipitation. The polymer was filtered out and cleaned by using MeOH, acetone and hexane soxhelt extraction and chloroform was used to dissolve the polymer. Removal of the chloroform resulted in the polymer P6 (molecular weight: 25200 g / mol, λmax=490 (film)).

example 2

Synthesis of Polymer P8

[0069]

[0070]Scheme 8 depicts the synthesis of compound P8. 0.3 mmol of m-TPT, 5.5 mg (2 mol %) of 5,5′-bis-trimethylstannyl-4,4′-bis(dodecyl)-2,2′-bithiophene, 14.6 mg (16 mol %) of tri(o-tolyl)phosphine and 5 mL of chlorobenzene were placed in a glass flask. After deoxygenation, the flask was placed in a microwave reactor (640 W, 30 min) for polymerization. After cooled to room temperature, the reaction mixture was added to methanol for precipitation. The polymer was cleaned by using MeOH, acetone and hexane soxhelt extraction and chloroform was used to dissolve the polymer. Removal of the chloroform resulted in the polymer P8 (molecular weight: 16900 g / mol, λmax=442 (film)).

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Abstract

The present invention discloses a soluble polythiophene derivative containing highly coplanar repeating units. The coplanar characteristic of the TPT (thiophene-phenylene-thiophene) units improves the degree of intramolecular conjugation and intermolecular π-π interaction. The polythiophene derivative exhibits good carrier mobility and is suitable for use in optoelectronic devices such as organic thin film transistors (OTFTs), organic light-emitting diodes (OLEDs), and organic solar cells (OSCs).

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a Continuation-In-Part of U.S. patent application Ser. No. 12 / 130,917, filed May 30, 2008, the disclosure of which is hereby incorporated by reference herein in its entirety. This Application claims priority of Taiwan Patent Application No. 097150001 filed on Dec. 22, 2008, the entirety of which is incorporated by reference herein.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The present invention relates to a soluble polythiophene derivative containing highly coplanar repeating units, and in particular relates to using the soluble thiophene derivative in optoelectronic devices.[0004]2. Description of the Related Art[0005]Recently, due to the fundamental semiconductor and optoelectronic properties of polymer semiconducting material, the material has attracted considerable research interest because of the potential for being used in optoelectronic devices such as organic thin film transistors (OTFTs), ...

Claims

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Application Information

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IPC IPC(8): C08G75/06
CPCC08G61/126Y02E10/549C08G2261/3223C08G2261/3241C08G2261/3243C08G2261/3246C08G2261/414C08G2261/91C08G2261/92C08G2261/95H01L51/0036H01L51/0043H01L51/0558H01L51/0037H01L51/0545H01L51/4253H01L2251/308C08G2261/148H10K85/1135H10K85/151H10K85/113H10K10/484H10K10/466H10K2102/103H10K30/50H10K30/30
Inventor CHAN, SHU-HUACHAO, TENG-CHIHKO, BAO-TSANCHEN, CHIH-PINGLIN, CHIN-SHENGCHEN, YI-LINGYU, CHAO-YING
Owner IND TECH RES INST
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